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Chemical Structure| 577-16-2 Chemical Structure| 577-16-2
Chemical Structure| 577-16-2

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CAS No.: 577-16-2

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2-Methylacetophenone is an endogenous metabolite.

4.5 *For research use only!

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Product Citations

Product Citations

Siriboe, Mary G ; Vargas, David A ; Fasan, Rudi

Abstract: Chiral cyclopropanols are highly desirable building blocks for medicinal chemistry, but the stereoselective synthesis of these molecules remains challenging. Here, a novel strategy is reported for the diastereo- and enantioselective synthesis of cyclopropanol derivatives via the biocatalytic asymmetric cyclopropanation of vinyl esters with ethyl diazoacetate (EDA). A dehaloperoxidase enzyme from Amphitrite ornata was repurposed to catalyze this challenging cyclopropanation reaction, and its activity and stereoselectivity were optimized via protein engineering. Using this system, a broad range of electron-deficient vinyl esters were efficiently converted to the desired cyclopropanation products with up to 99.5:0.5 diastereomeric and enantiomeric ratios. In addition, the engineered dehaloperoxidase-based biocatalyst is able to catalyze a variety of other abiological carbene transfer reactions, including N?H/S?H carbene insertion with EDA as well as cyclopropanation with diazoacetonitrile, thus adding to the multifunctionality of this enzyme and defining it as a valuable new scaffold for the development of novel carbene transferases.

Alternative Products

Product Details of [ 577-16-2 ]

CAS No. :577-16-2
Formula : C9H10O
M.W : 134.18
MDL No. :MFCD00008734
InChI Key :YXWWHNCQZBVZPV-UHFFFAOYSA-N
Pubchem ID :11340

Safety of [ 577-16-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H227
Precautionary Statements:P210-P261-P271-P280-P302+P352-P304+P340-P312-P363-P370+P378-P403+P235-P501

Calculated chemistry of [ 577-16-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 41.6
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

17.07 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.87
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.97
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.2
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.1
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.64
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.15

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.29
Solubility 0.687 mg/ml ; 0.00512 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.95
Solubility 1.49 mg/ml ; 0.0111 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.09
Solubility 0.11 mg/ml ; 0.000818 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.72 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 1.0

Application In Synthesis [ 577-16-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 577-16-2 ]

[ 577-16-2 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 383-63-1 ]
  • [ 577-16-2 ]
  • [ 163266-02-2 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In methanol; for 2h;Reflux; General procedure: Referring to Scheme 1, to the appropriate acetophenone derivative (0.05 mol) and ethyltrifluoroacetate (0.075 mol) in methanol (20 mL), sodium methoxide solution (0.1 mol of Na + 15 mL ofCH3OH) was added dropwise at room temperature, and the mixture was refluxed for 2 h. After themethanol was evaporated under vacuum, the residue was dissolved in ethyl acetate (50 mL), washedwith 5% HCl (25 mL) and water (25 mL), and dried over sodium sulfate. After the solvent wasevaporated under vacuum, the corresponding compound II was obtained.
  • 2
  • [ 611-14-3 ]
  • [ 7287-82-3 ]
  • [ 577-16-2 ]
  • 3
  • [ 611-14-3 ]
  • [ 22927-13-5 ]
  • [ 7287-82-3 ]
  • [ 577-16-2 ]
  • 4
  • [ 577-16-2 ]
  • [ 611-14-3 ]
YieldReaction ConditionsOperation in experiment
91% With triethylsilane; indium(III) bromide; In chloroform; at 60℃; for 1h;Inert atmosphere; General procedure: To a freshly distilled CHCl3 solution (0.6 mL) in a screw-capped vial under N2 atmosphere, InBr3 (10.6 mg, 0.0300 mmol), aromatic ketone 4 (0.6 mmol) and Et3SiH (383 muL, 2.40 mmol) was successively added. The resulting mixture was stirred at 60 C (bath temperature) or room temperature, and monitored by TLC or GC analysis until consumption of the starting ketone. The reaction was quenched with H2O. The aqueous layer was extracted with CH2Cl2 (5 mL × 3), the organic phases were dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The crude product was purified by a silica gel column chromatography (hexane/AcOEt = 19/1) to give the corresponding alkylbenzene 5. 1-Cyano-4-[1-(triethylsiloxy)ethyl]benzene (5k): 85% yield; colorless oil; 1H NMR (500 MHz, CDCl3) delta 0.54-0.62 (m, 6H), 0.90-0.93 (m, 9H), 1.41 (d, 3H, J = 6 Hz), 4.90 (q, 1H, J = 6 Hz), 7.45 (d, 2H, J = 8 Hz), 7.61 (d, 2H, J = 8 Hz); 13C NMR (125 MHz, CDCl3) delta 4.7, 6.7, 27.0, 69.9, 110.5, 119.0, 125.8, 132.0, 152.3; MS (ESI): m/z 284 (M++Na); HRMS (ESI): Calcd for C15H23NNaOSi: 284.1447, Found: 284.1407.
  • 5
  • [ 577-16-2 ]
  • [ 163266-02-2 ]
YieldReaction ConditionsOperation in experiment
64% 1F-a 1-(2-Methylphenyl)-4,4,4-trifluorobutane-1,3-dione This intermediate was prepared from commercially available 2- methylacetophenone. The product obtained was a liquid which was isolated from the reaction mixture by extraction with a suitable solvent like Ethyl acetate. The evaporation of the solvent gave the diketo product in 64% yield which was used as such for the next step. IR (KBr) cm-1 at 1147 (aliphatic C=O), 1199 (CF3), 1458 (C-H) 1608 (aromatic C=O)
  • 6
  • [ 577-16-2 ]
  • [ 1332832-16-2 ]
  • 7
  • [ 577-16-2 ]
  • [ 611-14-3 ]
  • [ 64811-81-0 ]
  • [ 7287-82-3 ]
  • 8
  • [ 611-14-3 ]
  • [ 7287-82-3 ]
  • [ 42070-90-6 ]
  • [ 577-16-2 ]
YieldReaction ConditionsOperation in experiment
With [bis(acetoxy)iodo]benzene; chloro(5,10,15,20-tetrakis-(10-nitro-1,2,3,4,5,6,7,8-octahydro-1,4;5,8-dimethanoanthracen-9-yl)porphyrin) iron(III); In methanol; dichloromethane; water; for 2h;Inert atmosphere; General procedure: Iron porphyrin complex 5 (1.2 mg 1 mumol) and imidazole (0.34 mg, 10 mumol) were placed in a test tube under argon. Then, 1 ml of distilled CH2Cl2/MeOH/H2O mixture (0.5:0.4:0.1) was added, followed by ethylbenzene (106 mg, 1 mmol). PhI(OAc)2 (32 mg, 100 mumol) in 0.1 ml CH2Cl2 was added over a period of 1 h with a syringe-pump. After the addition of all the PhI(OAc)2, the reaction mixture was allowed to stir for an additional 1 h. The mixture was analyzed by GC for oxidation yield based on oxidant, 41 %, alcohol/ketone ratio, 83:17, and alcohol enantiomeric excess, 68 % (conditions used: 80 C (1 min), 1 C min-1 80-120 C, 2.5 C min-1 120-180 C). Polarimetric measurement of the oxidation product determined that (R)-(+)-1-phenyl ethanol was formed in excess. The reaction and analysis of the other substrates and catalysts in Table 3 were carried out in an identical manner with that used for ethylbenzene oxidation. Except for indane, the enantiomeric excess was determined by chiral HPLC with a Chiralcel OB-H column: n-hexane/isopropanol 95:5; flow rate: 0.5 ml min-1, detection: 220nm.
  • 9
  • [ 407-38-5 ]
  • [ 577-16-2 ]
  • [ 163266-02-2 ]
 

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